JP5125834B2 - 縮合系共重合体 - Google Patents
縮合系共重合体 Download PDFInfo
- Publication number
- JP5125834B2 JP5125834B2 JP2008183034A JP2008183034A JP5125834B2 JP 5125834 B2 JP5125834 B2 JP 5125834B2 JP 2008183034 A JP2008183034 A JP 2008183034A JP 2008183034 A JP2008183034 A JP 2008183034A JP 5125834 B2 JP5125834 B2 JP 5125834B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- allyl
- reaction
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229920001577 copolymer Polymers 0.000 title claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 53
- 238000009833 condensation Methods 0.000 claims description 29
- 230000005494 condensation Effects 0.000 claims description 29
- 125000000962 organic group Chemical group 0.000 claims description 27
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 11
- 241000790917 Dioxys <bee> Species 0.000 claims description 9
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 8
- -1 allyl compound Chemical class 0.000 description 106
- 238000006243 chemical reaction Methods 0.000 description 100
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 66
- 229910052760 oxygen Inorganic materials 0.000 description 66
- 239000001301 oxygen Substances 0.000 description 66
- 150000001875 compounds Chemical class 0.000 description 65
- 239000012038 nucleophile Substances 0.000 description 58
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 56
- 239000003054 catalyst Substances 0.000 description 55
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 44
- 239000002994 raw material Substances 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 125000003118 aryl group Chemical group 0.000 description 25
- 229910052763 palladium Inorganic materials 0.000 description 24
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 23
- 235000019441 ethanol Nutrition 0.000 description 22
- 239000003446 ligand Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 18
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 18
- 150000003623 transition metal compounds Chemical class 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- 125000004423 acyloxy group Chemical group 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VZUAUHWZIKOMFC-ARJAWSKDSA-N [(z)-4-acetyloxybut-2-enyl] acetate Chemical compound CC(=O)OC\C=C/COC(C)=O VZUAUHWZIKOMFC-ARJAWSKDSA-N 0.000 description 15
- 230000000269 nucleophilic effect Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 13
- 230000002411 adverse Effects 0.000 description 13
- 125000006165 cyclic alkyl group Chemical group 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000004104 aryloxy group Chemical group 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- 125000005110 aryl thio group Chemical group 0.000 description 9
- 230000001588 bifunctional effect Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 7
- 0 CC=C([C@]1C(C(C2)=*)=C(C)C(c(c(C)c3C(C(C*4)C=C)=N)ccc3C4=*)=CC1)I2=C Chemical compound CC=C([C@]1C(C(C2)=*)=C(C)C(c(c(C)c3C(C(C*4)C=C)=N)ccc3C4=*)=CC1)I2=C 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 101150003085 Pdcl gene Proteins 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical class 0.000 description 6
- 125000005587 carbonate group Chemical group 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000010948 rhodium Substances 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical class C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 125000000746 allylic group Chemical group 0.000 description 4
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 150000002816 nickel compounds Chemical class 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 150000002941 palladium compounds Chemical class 0.000 description 4
- 150000003058 platinum compounds Chemical class 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 3
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical class C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005937 allylation reaction Methods 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229950011260 betanaphthol Drugs 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 150000002504 iridium compounds Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- YHLVIDQQTOMBGN-UHFFFAOYSA-N methyl prop-2-enyl carbonate Chemical compound COC(=O)OCC=C YHLVIDQQTOMBGN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003284 rhodium compounds Chemical class 0.000 description 3
- 150000003304 ruthenium compounds Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000005156 substituted alkylene group Chemical group 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- XPXBEIHHQIYWSL-UHFFFAOYSA-N 1,1-dibutoxybut-1-ene Chemical compound CCCCOC(=CCC)OCCCC XPXBEIHHQIYWSL-UHFFFAOYSA-N 0.000 description 2
- BVOSSZSHBZQJOI-UHFFFAOYSA-N 1-Hexen-3-ol Chemical compound CCCC(O)C=C BVOSSZSHBZQJOI-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- TXZQXWQFHSSVPI-UHFFFAOYSA-N 1-phenoxybut-1-enyl acetate Chemical compound CCC=C(OC(C)=O)OC1=CC=CC=C1 TXZQXWQFHSSVPI-UHFFFAOYSA-N 0.000 description 2
- IELYMBBIHQDONA-UHFFFAOYSA-N 1-prop-2-enoxyoctane Chemical compound CCCCCCCCOCC=C IELYMBBIHQDONA-UHFFFAOYSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 2
- GGXSDQDNOMWAFV-UHFFFAOYSA-N 2-bromo-1h-pyridin-4-one Chemical compound BrC1=CC(=O)C=CN1 GGXSDQDNOMWAFV-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- GYLKKXHEIIFTJH-UHFFFAOYSA-N 3-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC(C#N)=C1 GYLKKXHEIIFTJH-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- AXMYIANZGNOXHL-UHFFFAOYSA-N 4-but-1-enoxybutyl acetate Chemical compound CCC=COCCCCOC(C)=O AXMYIANZGNOXHL-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
- LYJHVEDILOKZCG-UHFFFAOYSA-N Allyl benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1 LYJHVEDILOKZCG-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XXIKYCPRDXIMQM-UHFFFAOYSA-N Isopentenyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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Landscapes
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Description
ることによって進行する。
本発明に係るアリル化合物の製造方法(以下、適宜「本発明の製造方法」と略称する。)は、後述する特定の遷移金属化合物と、同じく後述する多座配位ホスファイト化合物とを含む触媒の存在下、アリル原料化合物と酸素求核剤とを反応させることによって、該アリル原料化合物とは異なる組成式を示す新たなアリル化合物を製造するものである。
アリル原料化合物は、分子内にアリル基と脱離基とを有するものであれば特に制限されないが、全体の分子量として1500以下のもの(炭素数で約100以下のもの)であり、反応条件下において全量又は一部のアリル原料化合物が、溶媒への溶解、酸素求核剤との相溶、若しくは熱による融解等によって、溶けた状態になり得るものが好ましい。中でも、下の一般式(a)で表わされる、Ra〜Reで表される基を有するアリル基にXで表される脱離基が結合した構造の化合物が好ましい。なお、脱離基とは、母体となる基質骨格(本発明ではアリル骨格)の炭素に結合していて、一般的に電子吸引性基で、電子対を持って基質分子から離れていく原子又は原子団のことを指す。
上記例示の中でも、Ra〜Reとしては、それぞれ独立に、水素原子、無置換又は置換のアルキル基、無置換又は置換のアリール基が好ましい。
アミノ基、RSO2−で表わされるスルホニル基、RSO2O−で表わされるスルホネイト基、RC(=O)O−で表わされるアシロキシ基、R’OC(=O)O−で表わされるカーボネイト基、R’NHC(=O)O−で表わされるカルバメイト基、(R’O)2P(=O)O−で表わされるホスフェイト基、RO−で表わされるアルコキシ基又はアリーロキシ基を表わす。なお、前記各式中におけるRは一価の有機基を表わし、R’は水素原子又は一価の有機基を表わす。有機基としては、反応系に悪影響を及ぼす虞のないものであれば、その種類は特に制限されないが、アルキル基又はアリール基等が好ましい。R及びR’が有機基である場合の炭素数は、通常40以下、好ましくは30以下、更に好ましくは20以下である。これらの例示基のうちアミノ基、スルホニル基、スルホネイト基、アシロキシ基、カーボネイト基、カルバメイト基、ホスフェイト基、アルコキシ基、又はアリーロキシ基は、更に上記置換基を有していても良い。なお、脱離基Xが炭素鎖を含む基である場合は、その炭素鎖中に一以上の炭素−炭素二重結合又は三重結合が存在していても良い。
アリルアルコール類の具体例としては、2−ブテニルアルコール、2,3−ジメチル−2−ブテニルアルコール、3−ブロモアリルアルコール、シンナミルアルコール、クロチルアルコール、3−メチル−2−シクロヘキセン−1−オール、3−メチル−2−ブテン−1−オール、ゲラニオール、2−ペンテン−1−オール、3−ブテン−2−オール、1−ヘキセン−3−オール、2−メチル−3−フェニル−2−プロペン−1−オール、1−アセトキシ−4−ヒドロキシシクロペンテン−2、1,2−ジヒドロカテコール、3−ヘキセン−2,5−ジオール等が挙げられる。
ニトロアリル類の具体例としては、1−ニトロ−2−ブテン、1−ニトロ−1,3−ジフェニルプロペン、3−ニトロ−3−メトキシプロペン等が挙げられる。
アリルスルホン類の具体例としては、アリルフェニルスルホン、メチリル−p−トリルスルホン、2−メチル−3−スルホレン、1,3−ジフェニルアリルメチルスルホン等が挙げられる。
アリルスルホネイト類の具体例としては、アリルトルエン−4−スルホネイト、3−チオフェンメタンスルホネイト、4−クロロ−2−ブテニルメタンスルホネイト等が挙げられる。
アリルカルバメイト類の具体例としては、アリル−N−(4−フルオロフェニル)カルバメイト、2−ブテニル−N−メチルカルバメイト、フルフリル−N−(2−メトキジフェニル)カルバメイト等が挙げられる。
アリルエーテル類の具体例としては、アリルエチルエーテル、アリルフェニルエーテル、2,3−ジフェニルアリルイソプロピルエーテル、2−ブテニル−4−フルオロフェニルエーテル等が挙げられる。
ビニルエチレンオキシド類の具体例としては、ブタジエンモノオキシド、シクロペンタジエンモノオキシド、1,3−シクロヘキサジエンモノオキシド等が挙げられる。
上記一般式(b)中、R1,R2は、それぞれ独立に、アセトキシ基又はヒドロキシ基を表わす。上記一般式(b)で表わされる3,4−二置換ブテン−1の具体例としては、3,4−ジアセトキシブテン−1、3−アセトキシ−4−ヒドロキシブテン−1、4−アセトキシ−3−ヒドロキシブテン−1、及び3,4−ジヒドロキシブテン−1が挙げられる。
上記一般式(c)中、R3、R4は、それぞれ独立に、アセトキシ基又はヒドロキシ基を表わす。上記一般式(c)で表わされる1,4−二置換ブテン−2の具体例としては、1,4−ジアセトキシブテン−2、1−アセトキシ−4−ヒドロキシブテン−2、及び1,4−ジヒドロキシブテン−2が挙げられる。
求核性酸素原子と窒素原子で結合する有機基としては、無置換又は置換のアミノ基、C=N結合を有する基等が挙げられる。
求核性酸素原子とリン原子で結合する有機基としては、無置換又は置換のホスホネイト基、無置換又は置換のホスフィネイト基、もしくは無置換又は置換のホスフィノイル基等が挙げられる。
なお、上記各例示基の置換基としては、反応系に悪影響を及ぼす虞のないものであれば特に制限されないが、ハロゲン原子、ヒドロキシ基、アミノ基、ホルミル基、シアノ基、ニトロ基、鎖状又は環状のアルキル基、アリール基、アルコキシ基、アリーロキシ基、アシル基、アシロキシ基、アルキルチオ基、アリールチオ基、パーフルオロアルキル基、トリアルキルシリル基、アルコキシカルボニル基、又はアリーロキシカルボニル基等が好ましい。上記各例示基がこれらの置換基を有する場合には、置換基も含めた炭素数が上記範囲内となるようにする。
は、アリル原料化合物の異性化物が生成物として得られるのみという状態となるので、そのような酸素求核剤は除外される。また、酸素求核剤がアリル原料化合物と全く同じ場合、例えば酸素求核剤とアリル原料化合物が共にアリルアルコールであるような場合には、従来技術の項で記載しているように得られる生成物は原料が単に脱水縮合したような構造であるジアリルエーテルに限られ、幅広い合成を行なう観点から見ると重要性に欠けるので、そのような酸素求核剤も除外される。
Aが求核性酸素と炭素原子で結合した有機基である場合には、ヒドロキシ化合物類、カルボン酸類、チオカルボン酸類、又はセレノカルボン酸類等が挙げられる。
ヒドロキシ化合物の具体例としては、メタノール、エタノール、n−プロパノール、n−ブタノール、sec−ブタノール、t−ブタノール、アリルアルコール、2−エチルへキシルアルコール、4−クロロ−1−ブタノール、ベンジルアルコール、シクロヘキサノール、エチレングリコール、1,3−プロパンジオール、及び1,4−ブタンジオール等のアルコール類;フェノール、p−メトキシフェノール、2,4−ジメチルフェノール、1−ナフトール、2−ナフトール、3,6−ジ−t−ブチル−2−ナフトール、2−ピリジノール、又は2−ブロモ−4−ピリジノール等のフェノール類;及び2−ピリジノール、2−ブロモ−4−ピリジノール等の水酸基を有するヘテロアリール化合物が挙げられる。
チオカルボン酸類の具体例としては、CH3C(=S)−OHで表わされる化合物、又はPhC(=S)−OHで表わされる化合物等が挙げられる。
セレノカルボン酸類の具体例としては、CH3(C=Se)−OHで表わされる化合物、又はPhC(=Se)−OHで表わされる化合物等が挙げられる。なお、本明細書において、Phはフェニル基を表わす。
が挙げられる。ロジウム化合物としては、RhCl3、Rh(OAc)3、[Rh(OAc)2]2、Rh(acac)(CO)2、[Rh(OAc)(cod)]2、[RhCl(cod)]2等が挙げられる。イリジウム化合物としては、IrCl3、Ir(OAc)3、[IrCl(cod)]2が挙げられる。ニッケル化合物としては、NiCl2、NiBr2、Ni(NO3)2、NiSO4、Ni(cod)2、NiCl2(PPh3)3等が挙げられる。パラジウム化合物としては、Pd(0)、PdCl2、PdBr2、PdCl2(cod)、PdCl2(PPh3)2、Pd(PPh3)4、Pd2(dba)3、K2PdCl4、K2PdCl6、PdCl2(PhCN)2、PdCl2(CH3CN)2、Pd(dba)2、Pd(NO3)2、Pd(OAc)2、Pd(CF3COO)2、PdSO4、Pd(acac)2、その他、カルボキシレート化合物、オレフィン含有化合物、Pd(PPh3)4等のような有機ホスフィン含有化合物、アリルパラジウムクロライド二量体等が挙げられる。白金化合物としては、Pt(acac)2、PtCl2(cod)、PtCl2(CH3CN)2、PtCl2(PhCN)2、Pt(PPh3)4、K2PtCl4、Na2PtCl6、H2PtCl6が挙げられる。なお、以上の例示において、codは1,5−シクロオクタジエンを、dbaはジベンジリデンアセトンを、acacはアセチルアセトネイトを、Acはアセチル基をそれぞれ表す。
置換基を有しても良いジアリーレン基の具体例としては、下記式(A−1)〜(A−48)で表わされる構造の基が挙げられる。
本発明の縮合系共重合体におけるAとA’との存在量比は特に限定されないが、Aのユニットの方が多くなる傾向があり、具体的には、A:A’(モル比)の値が通常1:10以上、好ましくは1:2以上、より好ましくは1:1以上であって、通常10:1以下、好ましくは5:1以下、より好ましくは3:1以下である。
本発明の縮合系共重合体の末端構造は、縮合系共重合体の末端ユニットがA又はA’のブテンジイルユニットである場合には、アセトキシ基又はヒドロキシ基であり、縮合系共重合体の末端ユニットがB、B’又はB”のジオキシユニットである場合には、水素原子である。
アリル原料化合物としてアリルメチルカーボネイトを用い、酸素求核剤としてフェノールを用いたアリルフェニルエーテルの合成反応に本発明を適用した。
アリル原料化合物として酢酸アリルを用い、酸素求核剤として1−オクタノールを用いたアリルオクチルエーテルの合成反応に本発明を適用した。
アリル原料化合物として酢酸アリルを用い、酸素求核剤として安息香酸を用いた安息香酸アリルの合成反応に本発明を適用した。
アリル原料化合物としてcis−1,4−ジアセトキシ−2−ブテンを用い、酸素求核剤として1−ブタノールを用いたブチルブテニルエーテル類の合成反応に本発明を適用した。
アリル原料化合物としてcis−1,4−ジアセトキシ−2−ブテンを用い、酸素求核剤としてフェノールを用いたフェニルブテニルエーテル類の合成反応に本発明を適用した。
アリル原料化合物としてcis−1,4−ジアセトキシ−2−ブテンを用い、酸素求核剤として二官能性カルボン酸であるアジピン酸を用いた不飽和結合含有ポリエステルオリゴマーの合成反応に本発明を適用した。
アリル原料化合物としてcis−1,4−ジアセトキシ−2−ブテンを用い、酸素求核剤として二官能性アルコールである1,4−ブタンジオールを用いた不飽和結合含有ポリエーテルオリゴマーの合成反応に本発明を適用した。
アリル原料化合物としてcis−1,4−ジアセトキシ−2−ブテンを用い、酸素求核剤として二官能性フェノールである2,2−ビス(4−ヒドロキシフェニル)プロパン(通称:ビスフェノールA)を用いた不飽和結合含有ポリエーテルオリゴマーの合成反応に本発明を適用した。
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